I use a Sansa Fuze; it has a config setting which allows one to set whether, when its USB cable is connected to a computer, it appears to the computer just as a disk drive, or some other thing I've never explored.
I plug it in, see the folders etc, copy files, and dismount (ie 'safely remove') it. It sees its been disconnected from the computer and that something has changed and takes a minute or so to rebuild its index. And that's that.
I think lots of MP3 players do this sort of thing... provided they are not Apple ones. You need to read reviews of them on eg Amazon, as other people will mention how this is done.
I have never in my life used iTunes. I collect mp3s from various podcasts (subscribed to using a Windows program named Juice), and radio programmes from the BBC (using the Windows version of get_iplayer - which is mainly known as a Linux app but works on Windows too), and by ripping CDs (using Windows Media Player), and sometimes I even buy them from Amazon.
As you would expect, the world according to apple revolves around itunes. If you add you tracks to that first, it should be able to sync them with the ipod.
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